


Late Night Doughnuts

by retro_pretzel



Category: Gilmore Girls
Genre: F/M
Language: English
Status: Completed
Published: 2017-06-13
Updated: 2017-06-13
Packaged: 2018-11-13 20:54:05
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,604
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11193210
Author URL: https://archiveofourown.org/users/retro_pretzel/pseuds/retro_pretzel
Summary: Set immediately after the revival ends.





	Late Night Doughnuts

**Author's Note:**

> I don't own anything blah blah blah disclaimer.

“Mom, I’m pregnant.”  
Rory regretted the instant the words left her mouth. What was she thinking? It was her mother’s wedding day. Selfish. If there was anything she should include in the book, it was how timing was not the Gilmores’ strong suit.  
A long silence passed between Lorelai and Rory on the gazeebo. Rory saw the meaning of what she had just said travel like a storm across her mother’s face. She aged ten years in an instant. Her shoulders sank, then lifted. She rose and kissed Rory on the forehead, her face impassable again.  
Without saying a word, Lorelai turned to walk back towards the house. Rory understood. Not now. Not today. Another time, she could begin to process the words, begin to formulate a plan. Today, there was a wedding. Tomorrow, there was time.  
The real (fake?) wedding night was just as beautiful as the previous night had been. Stress free, just like Luke had hoped. Full of friendship. The wedding party was small, just Jess and herself for attendants. Rory chose a simple black cocktail dress with a high-low skirt made from taffetta. Jess stood across from her in the best man slot in a suit. Too warm for a jacket, he got by with just shirt sleeves and a vest. He made no eye contact with Rory across the aisle. Not that she expected him to, she chided internally.  
After the ceremony was over, Liz paraded Jess around to anyone and everyone who would listen, declaring him the most handsome man at the wedding. Rory did happen to catch her re-introducing him to Taylor as “her son, the handsome and accomplished publisher,” and Taylor loudly pretending not to remember Jess’s time in Stars Hollow. Rory snorted into her drink.  
Of course the worst part about her pregnancy was how much she wished she could have been blissfully drunk. As it were, soberness had the effect of making it feel like she was dredging painfully through a swamp while everyone around her spun at 100 miles an hour. She wished to be able to forget, to be spinning with them, even for a moment. The result was dizzying either way.  
Paris was the only other person who knew about her condition. Rory told her a few days before she had told Lorelai. She was surprisingly not judgemental, which Rory could only assume was a softening of her own motherhood.  
“You know, I could set you up with a family,” she suggested almost too quickly. “It’s not something I normally do, but I know people with contacts. A healthy spawn of two Yale graduates would be in high demand.”  
Rory told her she’d mull it over. It was still early. Paris promised at the very least, she could get Rory the best prenatal care in the northeast, and Rory knew she meant it.  
After three champagne toasts (a quick sip; the glass down), two disastrous flash mobs (Rory didn’t think Luke really understood the concept there), and several, several pieces of wedding cake (Sookie couldn’t decide, so she insisted that they all be consumed) the wedding finally ended. Lorelai and Luke walked through a tunnel of sparklers and back towards the house. Rory turned to head towards the diner.  
In order to give her mom and Luke a proper wedding night, Rory had set a bag and a blow up mattress upstairs in the diner the day before The plan was to stay the night there and meet Lorelai and Emily for brunch in the morning. And, she cocked a half smile, late-night doughnuts.  
Rory kicked off her heels upstairs and pulled her Yale sweatshirt over the gauzy black bridesmaids dress. It smelled of cedar and cigars, still a bit like her grandfather’s study. Her stockings had ripped at some point during the night, but she paid them no mind. Her feet made soft sounds coming back down the stairs. Right before the bottom stair, though, a small noise made her stop.  
The diner had always felt like a second home to Rory, but at night, maybe it was a little larger and more drafty than she’d remembered. Street light moved in between the cracks and created movement and the uncomfortable feeling of being observed. Calm your breathing, she reminded herself. It’s probably just the stove creaking, like stoves tend to do. But no, she heard it again. The entrance bell annouced a presence. Rory’s heartbeat quickened. She reached for the baseball bat Luke hid at the entrance to the staircase and crept around the corner.  
Of all the ominous shapes her mind conjured, the figure at the door was definitely dark, but smaller at least in stature. Her eyes adjusted and made out the familiar silouette against the door.  
“Jess!” she screamed, still brandishing the baseball bat. He spun, startled, to face her.  
“Jesus Christ, Gilmore! Why are you here?!”  
“Why are you here?!”  
“I live here! I lived here! I did. Once. Live here.” Jess stumbled, his hands in the air. “Will you please put the baseball bat down?”  
Rory realized she had been creeping closer, bat still in hand. “Oh. Of course.”  
She laughed, relieved, and collapsed into a chair.  
Jess relaxed too. He put his coat on the coat rack.  
“Coffee?” Rory offered. She began to put a pot on.  
“You do know it’s midnight, right?” Jess protested. She gave him a sideways glance. He shrugged, handing her two mugs.  
“I’m sorry I barged in on you like this. I didn’t know you’d be here. It was late, and I had a few drinks. My plan was to drive back to Liz and TJ’s, but- I didn’t think anyone would be here,” he finished.  
“Oh, I was just trying to give Mom and Luke some privacy,” Rory explained. “I can head back home though if you need to sleep here.”  
“No, no, no,” Jess protested. “I’ll sober up here and head back. Just make mine black.” He winked, and put a hand on her waist as he moved around her to the other side of the counter. Rory felt a flash of heat in her chest. It’d been a minute since anyone had touched her in a familiar way, even innocently. It sent a shockwave through her. Not to mention, pregnancy hormones. How embarrassing. She shook it off and tossed him a bagel.  
For about an hour, they sat and ate and talked. She mostly asked questions about his life and the book store, uneasy to reveal too much about her own fiasco of a life the past few months. She did tell him about the book, about writing it in her grandfather’s study. About the funeral and Emily’s transformation since then. About the drunk in London and the failed book collaboration.  
He told her stories of drunk poetry readings his friends had hosted, where the poets were required to dress in drag. Long nights up editing in New York. Ridiculous stories of Liz and TJ and the new baby, who hardly warranted the title “baby” anymore. Before long, they were both laughing so hard they were crying. Rory pretended not to notice he was sneaking extra shots of whiskey into his coffee. He finally offered her one. She declined.  
Soon, they reached a silence. Rory thought for a moment. Warmed her hands on her coffee mug. “Can I ask you a question?” she posed  
“Sure,” Jess said.  
“Why have you been avoiding me?”  
Jess went quiet. He licked his bottom lip and thought. Finally, he said, “Can I answer a question with a question?”  
Rory leaned in.  
“Why are you here fucking around with the Stars Hollow Gazette?”  
Rory froze. That’s not what she was expecting.  
“I don’t see what’s wrong with the Stars Hollow Gazette,” she said defensively. “It’s work and it’s news. So what if it’s not New York or the White House or wherever people think I should be? And I have the book now, so...” she trailed off and took a swig of her coffee. Jess was taking it all in.  
“It’s not that I don’t think the book is going to be good,” Jess began. “Of course I do, or I wouldn’t have suggested it. Nor am I suggesting that the Stars Hollow Gazette isn’t a worthwhile pursuit, but-” he paused.  
“But what?” Rory dared.  
“Rory. You’re better than this. You know it. And it’s not just moving home. Lots of people do that. It’s just- Luke’s told me. You’ve had a lot of opportunities. You could easily be doing what you want to do. Why this?”  
“Is that why you’ve been avoiding me? Because you think I’m beneath you now? I haven’t lived up to your teenage fantasy standards?” Now, a different fire was lit in her.  
Jess attempted to back pedal. “Teenage fantasy standards? Whoa. That’s not what I’m saying. And who said I was avoiding you to begin with?”  
“You have been. I can tell. I’ve seen you three times since I’ve moved back to Stars Hollow, and only once have you managed to have a real conversation with me. Every time I come home and you’re there, you find some excuse to leave. This is the first time in a year you’ve managed to look me in the eye!”  
Without realizing it, she had stood and was yelling. Jess didn’t seem surprised, but Rory had a hard time making out the emotion on his face. He said nothing, so she continued.  
“You think it was easy for me growing up like this? Everyone constantly sacrificing themselves on the altar of Rory Gilmore? I’m everyone’s last hope! My mother wasted her youth raising me. My grandparents fell over themselves to make everything so easy. The fucking town!” she paused at this.  
“There was a god damned party over how great I was. Do you have any idea what’s that’s like? Do you know how much pressure that is? And I didn’t even want it! Or at least, I thought I did, but now I don’t know what I want. All I really want is not to feel even the least bit powerless, but I can’t stop. I can’t stop taking. It’s so selfish, and it’s all I know how to do!”  
Rory breathed in heavy and collapsed back on the chair with a quiet sob. How long had that volcano lay dormant?  
“I’m not special,” she muttered into her coffee. There was a long pause as she sipped.  
“I know that,” Jess replied. Rory looked up, surprised.  
“You did?”  
“Of course I did.” His voice was measured.  
“I don’t believe in special. But if you think I feel sorry for you for one minute, you’re in the wrong place. Wait. Let me finish.” He held up a hand to cut off her attempted protest.  
“If you had wanted someone to make you feel better, you could have called Lane or your mother or anyone. You told me all this because you needed a swift kick in the ass. You know it. I mean, why the hell did you want to start writing in the first place?”  
Rory was dumbfounded. “What do you mean why?”  
“I mean tell me why you wanted to write.” he repeated. She thought.  
“I mean, there’s lots of reasons. I was good at it, I guess. I wanted to make my family proud.”  
“That’s not a reason to write,” Jess responded firmly. “That’s a reason to write at Yale. You could have done anything- literally anything- to make your family proud. Why writing?”  
Rory paused again.  
“I suppose,” she began, “I suppose I wanted to help people.”  
“Help people with what?”  
“Well.” She wrestled a moment with her thoughts. “When I was a kid, I was lonely a lot. I didn’t make friends easily. I started reading books to feel less lonely. I connected to the characters.”  
Jess nodded. This was a thing he understood. Rory continued.  
“And I got older and started reading magazines and newspapers. I connected to actual people. Everyone in Stars Hollow thinks a lot the same way, you know? That’s why they’re here. They want this world that never changes. It has its benefits. But once you realize how much bigger the world is out there, it’s hard to go back, isn’t it? I was reading so many other perspectives from people who didn’t live like me. Empathizing with people from all over the world. I wanted other people to see the world like I saw it. Which is to say that I wanted other peoples’ voices to be heard. I wanted to connect people.”  
“When’s the last time you felt like you were doing that? When’s the last time, besides the book, that you didn’t feel like you were writing for a byline?” Jess asked.  
Rory paused.  
“Maybe a few years after the Obama campaign bus. I was working as a part-time reporter at this little news outlet in New York. Doing freelance stuff on the side, and writing for a Brooklyn monthly. We did a story on mandatory minimums and a woman who had been sentenced to ten years for a minor offense went free because of our coverage. People showed up to cheer her when she was released. Total strangers paid for her daughter to go to college. Totally changed their lives. I did a ton of research and co-edited, but the byline didn’t actually go to me in the end. I didn’t even mind.”  
“What happened to that?” Jess asked.  
Rory frowned at the memory. What had happened to that is that she flew to London with her grandmother for a week and bumped into Logan. He convinced her that she was wasting her time not devoting everything to freelance writing. She could afford to live without steady income for a bit, and she could get bylines in the major publications, he reasonsed. Then, she took the afternoon off from Emily Gilmore, and they fucked in the bed he shared with the dutchess. God, she was awful.  
The New Yorker piece had come out of that, but she missed breaking stories. She missed being part of a team. And maybe she hadn’t even fully realized how much until now.  
“It didn’t work out,” she said, flatly.  
“And are you doing what you want at the Gazette?” he asked.  
“No,” she conceded. “I’m doing the fucking fall poem.”  
Jess sighed.  
“If you think I’ve been avoiding you, it’s because I can’t watch you do this to yourself,” Jess said as he stood. “I can’t spend any more time being the person that you run to when you need fixing. You think you’re selfish? You think everything’s too easy for you because your family feels guilty over you not having a dad? You expect me to feel any sympathy for you?”  
“Dammit, Rory. You’re mom didn’t go through everything she did because you were special and you needed to live up to some sort of special standard. She did it because she’s a mom, and she wanted you to have a choice. If there’s anything you’re really feeling guilty about, it’s being afraid to get out there and do the damn thing! Write the piece you don’t want to write to get to the pieces you do. Take the job that gets you the next job. Don’t come back here with your tail tucked between your legs because someone out there gave you a B minus.”  
“Now hang on,” Rory insisted. “It was several B minues in a row.”  
Jess charged onward.  
“You want to know why I’m avoiding you? It’s not because you didn’t live up to some realistic expectation. I read your last couple of pieces. There’s nothing of you in them. You’re taking the coward’s way out, and that’s not the Rory I know.”  
Jess took a long breath and ran both hands through his hair.  
Rory was crying and laughing now. The irony of the situation was too much. Jess paced a few feet and spun to face her.  
“What’s funny?” he yelled. He hadn’t realized how loud he’d gotten. She shreiked a laugh again.  
“You sound like Paris.”  
“Yeah?!” Jess yelled, exasperated. “Well! I always liked her!”  
“There’s more.” she laughed, tears streaming freely now.  
“What else could there possibly be?”  
“I’m pregnant, Jess.” she said. It was practically the funniest joke she’d ever told.  
The air was sucked from the room. Jess stared at her, wide-eyed. He put his hands down and came back towards her, biting his bottom lip.  
“Pregnant?” he repeated, with a low whistle.  
“Pregnant,” she confirmed. Another silence.  
“That guy you were seeing..?” he postured.  
“Who? Oh. No. Not Paul.”  
“Then...” Jess’s eyes opened in realization.  
“Logan, probably.” she sighed.  
“The dick from Yale? I thought he was married to some dutchess.”  
Rory said nothing, and looked to the side. She was sick of explaining this.  
“I see,” Jess conceded, following her gaze.  
“I mean, it could be the Wookie’s.” she chuckled. He gave her a half-hearted chuckle in reply, but of course, he didn’t get the joke.  
“I didn’t mean to start this tonight,” Jess said, taking a seat again. “Don’t listen to me. I don’t know how to live your life. I’m just as fucked up as we all are.”  
“You really aren’t ever scared, are you?” Rory asked, as if she were seeing him for the first time.  
“That’s not true,” Jess replied. “You think I’m so different from you and Yale Douche, but I get it. I just had a hell of a lot less to lose starting out.”  
After a long minute, he stood again.  
“I should go. It’s almost 3am. I can get to Liz’s before sun up.”  
He moved to grab his jacket, and suddenly Rory’s heart was bursting from her chest. He was right. He was always ahead of her. Logan would give her anything she wanted whenever she wanted, but it came with strings, and she knew that. He, like Mitchum, liked to be in control. And for so long, Rory felt like she deserved that. Maybe some weird version of Stockholm Syndrome. But Jess was different. He couldn’t give her a private plane to London or an apartment in the city, but he was patient and kind and honest, and he understood her more than anyone. Suddenly, she was desperate to keep him. So strong was the burst of emotion, that she almost lunged at the door to keep him from going out. He caught her, half falling over a chair leg.  
Terrified any hesitation would weaken her resolve, she cupped Jess’s face in her hands and pulled him in for a kiss before fully standing up again. Her tears on her lips mixed with his tongue, and she tasted whiskey and salt.  
It took an ungodly amount of time for him to kiss back, but finally, he put his hands on her cheeks and pulled her closer. Rory relaxed and breathed him in. She wrapped herself into him and started to slide a hand up his shirt. His hand caught her wrist though, and he pulled away, opening his eyes and looking stunned.  
“Rory, I can’t.” he whispered, putting his forehead against hers.  
Rory deflated. There was that feeling again. Stupid.  
“Of course,” she backed away a step. “But,” she said, blinking back tears. “You’ve still been drinking. You shouldn’t- You should-” She was floundering. “Can you stay with me?”  
Jess fingered the hem of his jacket for a long moment. He looked away, nodded, resigned, and followed her upstairs. 

Rory slipped out of her bridesmaid dress under the Yale sweatshirt. She pulled off her stockings, and climbed on the air mattress. Jess dressed down to his white undershirt and borrowed a pair of flannel pants from Luke’s drawer. Heat wasn’t running upstairs, and the attic felt drafty.There was a moment of polite hesitation and gesturing about maybe one of them sleeping on the floor, but the chill decided for them. Jess laid down next to her.  
Rory huddled up close and traced a line on his bicep with her finger.  
“When did you start working out?” she questioned, innocently.  
“A while ago,” he answered. “Just a thing I started doing to blow off steam. I didn’t think it’d actually stick,” he admitted.  
Rory shrugged.  
“I took up tap dancing,” she said with a yawn.  
“Of course you did,” Jess answered.  
It took Jess at least an hour to fall asleep after they had laid down. Rory’s head rested on his shoulder, and she fell asleep instantly, but he stayed awake, examining her eyelids, her lashes, the cracks in her lips, trying to remember the details. 

A few hours later, Jess awoke to a rattling doorknob. Pink sun was just starting to peek through the upstairs window. Jess rubbed sleep out of his eyes, and just as he was piecing together that it was probably Caesar at the door, Luke busted in. He froze in is tracks, seeing Jess.  
“Is that...?” he hissed low, pointing at Rory, still asleep.  
“What are you doing here? You’re supposed to be on a honeymoon!” Jess hissed back.  
“Caesar needed mustard!” he quipped, as if this explained everything.  
Rory suddenly stirred and rolled over, letting out a long sleepy sigh. Jess and Luke collectively held their breath until she settled again, an arm draped over Jess’s midsection.  
Jess pantomimed annoyedly for him to leave.  
Luke grabbed a case of mustard and frantically gestured wildly back his confusion with one arm, but then rolled his eyes and gave up.  
“‘I’m hearing about this later!” he hissed, and tip-toed back downstairs.


End file.
